JP3753255B2 - オルガノシリコン化合物の製造方法 - Google Patents
オルガノシリコン化合物の製造方法 Download PDFInfo
- Publication number
- JP3753255B2 JP3753255B2 JP27456293A JP27456293A JP3753255B2 JP 3753255 B2 JP3753255 B2 JP 3753255B2 JP 27456293 A JP27456293 A JP 27456293A JP 27456293 A JP27456293 A JP 27456293A JP 3753255 B2 JP3753255 B2 JP 3753255B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- carbon atoms
- group
- platinum
- silicon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 229910052697 platinum Inorganic materials 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000003058 platinum compounds Chemical class 0.000 claims description 13
- 150000001993 dienes Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003377 silicon compounds Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000005046 Chlorosilane Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910003480 inorganic solid Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000003544 oxime group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- -1 polysiloxane Polymers 0.000 description 27
- 238000006459 hydrosilylation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- KLFRPGNCEJNEKU-FDGPNNRMSA-L (z)-4-oxopent-2-en-2-olate;platinum(2+) Chemical compound [Pt+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O KLFRPGNCEJNEKU-FDGPNNRMSA-L 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- RBVMDQYCJXEJCJ-UHFFFAOYSA-N 4-trimethoxysilylbutan-1-amine Chemical compound CO[Si](OC)(OC)CCCCN RBVMDQYCJXEJCJ-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 229910004013 NO 2 Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003060 catalysis inhibitor Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CHSOOADWBVJAOF-VOTSOKGWSA-N dichloro-[(E)-hex-1-enyl]-methylsilane Chemical compound CCCC\C=C\[Si](C)(Cl)Cl CHSOOADWBVJAOF-VOTSOKGWSA-N 0.000 description 1
- IYPLTVKTLDQUGG-UHFFFAOYSA-N dodeca-1,11-diene Chemical compound C=CCCCCCCCCC=C IYPLTVKTLDQUGG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005461 organic phosphorous group Chemical group 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- KGRJUMGAEQQVFK-UHFFFAOYSA-L platinum(2+);dibromide Chemical compound Br[Pt]Br KGRJUMGAEQQVFK-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XMRSTLBCBDIKFI-UHFFFAOYSA-N tetradeca-1,13-diene Chemical compound C=CCCCCCCCCCCC=C XMRSTLBCBDIKFI-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
- C07F7/0878—Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929223335A GB9223335D0 (en) | 1992-11-06 | 1992-11-06 | Hydrosilylation process |
| GB9223335.2 | 1992-11-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06239873A JPH06239873A (ja) | 1994-08-30 |
| JP3753255B2 true JP3753255B2 (ja) | 2006-03-08 |
Family
ID=10724684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27456293A Expired - Lifetime JP3753255B2 (ja) | 1992-11-06 | 1993-11-02 | オルガノシリコン化合物の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5359112A (fr) |
| EP (1) | EP0596646B1 (fr) |
| JP (1) | JP3753255B2 (fr) |
| DE (1) | DE69328606T2 (fr) |
| GB (1) | GB9223335D0 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19508459A1 (de) * | 1995-03-09 | 1996-09-12 | Wacker Chemie Gmbh | Verfahren zur Herstellung von Alkylsilanen mit sperrigen Alkylresten |
| DE19644561C2 (de) * | 1996-10-26 | 2003-10-16 | Degussa | Verfahren zur Herstellung von Fluoralkyl-Gruppen tragenden Silicium-organischen Verbindungen |
| US5977280A (en) * | 1997-11-05 | 1999-11-02 | Dow Corning Corporation | Terminating post cure with amino acid esters |
| DE19847786A1 (de) | 1998-10-16 | 2000-04-20 | Degussa | Vorrichtung und Verfahren zum Befüllen und Entleeren eines mit brennbarem sowie aggressivem Gas beaufschlagten Behälters |
| US6696538B2 (en) * | 1999-07-27 | 2004-02-24 | Lg Chemical Ltd. | Semiconductor interlayer dielectric material and a semiconductor device using the same |
| US6365696B1 (en) | 1999-12-17 | 2002-04-02 | Crompton Corporation | Process for producing epoxyorganosilicon compounds |
| US20040038048A1 (en) * | 2000-02-02 | 2004-02-26 | Lg Chemical Ltd. | Semiconductor interlayer dielectric material and a semiconductor device using the same |
| US20040096893A1 (en) * | 2000-11-16 | 2004-05-20 | Rabah Boukherroub | Functionalised silicon surfaces, and method for their production |
| CA2326043A1 (fr) * | 2000-11-16 | 2002-05-16 | National Research Council Of Canada | Surfaces de silicium fonctionnalise, et methode de production de ces surfaces |
| EP1306381B1 (fr) * | 2001-10-10 | 2012-09-12 | Evonik Degussa GmbH | Procédé d'hydrosilylation de composés aliphatiques insaturés |
| US6590117B1 (en) * | 2001-11-15 | 2003-07-08 | Crompton Corporation | Promoted hydrosilation reactions |
| US6822066B2 (en) * | 2002-11-18 | 2004-11-23 | Dow Corning Corporation | Organosiloxane resin-polyene materials |
| JP2008120975A (ja) * | 2006-11-15 | 2008-05-29 | Momentive Performance Materials Japan Kk | 付加反応用触媒 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE553159A (fr) * | 1955-12-05 | |||
| US3188299A (en) * | 1963-02-28 | 1965-06-08 | Gen Electric | Preparation of stable mixtures of organosilicon compositions in the presence of a nitrogen-containing ligand |
| DE1768785C3 (de) * | 1968-06-29 | 1975-01-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von OrganosiHciumverbindungen |
| US3795656A (en) * | 1973-01-02 | 1974-03-05 | Stauffer Chemical Co | Organosilicon compositions containing ammonium platinum adducts |
| US3925434A (en) * | 1975-01-22 | 1975-12-09 | Union Carbide Corp | The reaction of chlorosilanes with unsaturated organic compounds |
| DE3000768A1 (de) * | 1980-01-10 | 1981-07-16 | Wacker-Chemie GmbH, 8000 München | Verfahren zum anlagern von si-gebundenem wasserstoff an aliphatische mehrfachbindung |
| DE3131954C2 (de) * | 1981-08-13 | 1984-10-31 | Degussa Ag, 6000 Frankfurt | Metallkomplexe von polymeren, gegebenenfalls vernetzten Organosiloxanaminen, Verfahren zu ihrer Herstellung und Verwendung |
| DE3133869C1 (de) * | 1981-08-27 | 1983-05-05 | Th. Goldschmidt Ag, 4300 Essen | Verfahren zur Addition von organischen Siliciumverbindungen mit SiH-Gruppen an Verbindungen mit olefinischen Doppelbindungen |
| US4398010A (en) * | 1981-12-07 | 1983-08-09 | Sws Silicones Corporation | Method for accelerating the activity of a hydrosilation catalyst |
| US4417069A (en) * | 1983-02-22 | 1983-11-22 | General Electric Company | Method of preparing β-phenylethylchlorosilanes |
| DE3404703A1 (de) * | 1984-02-10 | 1985-09-05 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 3-chlorpropyltrichlorsilan |
| US4584361A (en) * | 1985-06-03 | 1986-04-22 | Dow Corning Corporation | Storage stable, one part polyorganosiloxane compositions |
| US5103033A (en) * | 1991-06-24 | 1992-04-07 | Dow Corning Corporation | Process for preparation of β-cyanoalkylsilanes |
| GB9126049D0 (en) * | 1991-12-07 | 1992-02-05 | Dow Corning | Hydrosilylation process |
| US5191103A (en) * | 1991-12-30 | 1993-03-02 | Union Carbide Chemicals & Plastics Technology Corporation | Process and composition for promoting hydrosilylation reactions using sterically hindered nitrogen-containing and phosphorus-containing compounds |
| US5258480A (en) * | 1992-05-18 | 1993-11-02 | General Electric Company | Syntheses of epoxysilicones |
| US5206402A (en) * | 1992-09-17 | 1993-04-27 | Dow Corning Corporation | Process for preparation of Ω-alkenylchlorosilanes |
-
1992
- 1992-11-06 GB GB929223335A patent/GB9223335D0/en active Pending
-
1993
- 1993-10-27 EP EP93308559A patent/EP0596646B1/fr not_active Expired - Lifetime
- 1993-10-27 DE DE69328606T patent/DE69328606T2/de not_active Expired - Lifetime
- 1993-11-02 JP JP27456293A patent/JP3753255B2/ja not_active Expired - Lifetime
- 1993-11-02 US US08/144,365 patent/US5359112A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69328606D1 (de) | 2000-06-15 |
| EP0596646A1 (fr) | 1994-05-11 |
| DE69328606T2 (de) | 2000-10-05 |
| US5359112A (en) | 1994-10-25 |
| GB9223335D0 (en) | 1992-12-23 |
| JPH06239873A (ja) | 1994-08-30 |
| EP0596646B1 (fr) | 2000-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5939576A (en) | Method of functionalizing polycyclic silicones and the compounds so formed | |
| JP3753255B2 (ja) | オルガノシリコン化合物の製造方法 | |
| KR20000048250A (ko) | 다수의 가수분해성 기와 함께 적어도 하나의 유기작용기를갖는 폴리오르가노실록산 | |
| JPH035489A (ja) | アミノプロピルシラン化合物の製造方法 | |
| JP6689005B2 (ja) | シクロジエン添加剤を使用する白金触媒ヒドロシリル化反応 | |
| JPS63179883A (ja) | 付加反応方法 | |
| EP3071585B1 (fr) | Catalyseurs de cobalt et leur utilisation pour l'hydrosylation et la silylation déshydrogénative | |
| JP4727006B2 (ja) | 置換されたシルエチレン基で部分的に末端をブロックされたポリジオルガノシロキサンの製造方法 | |
| JPH0353317B2 (fr) | ||
| US5270424A (en) | Hydrosilylation process | |
| JP2017520519A (ja) | ジアルキルコバルト触媒並びにヒドロシリル化および脱水素シリル化のためのそれらの使用 | |
| JP2000103859A (ja) | エポキシ基含有オルガノポリシロキサン又はエポキシ基含有オルガノシランの製造方法 | |
| JP3839498B2 (ja) | 白金−オルガノシロキサン錯体の調製方法 | |
| JPH0559072A (ja) | オレフイン系及びアセチレン系アザシラシクロペンタン並びにその調製方法 | |
| US3595733A (en) | Method of preparing alpha-unsaturated organosilicon compounds | |
| JPS6220194B2 (fr) | ||
| EP0768331A1 (fr) | Polymères de siloxane en feuille et tubulaire | |
| JP6878619B2 (ja) | アミノプロピルアルコキシシランの製造方法 | |
| Andrianov et al. | The Hydride Addition of Organohydrosiloxanes to Compounds with a Multiple Carbon–Carbon Bond | |
| JP5001981B2 (ja) | ヒドロシリル化法 | |
| KR20220079627A (ko) | 히드리도실리콘 화합물로부터 실록산을 제조하는 방법 | |
| US6118014A (en) | Organofunctional cocyclic siloxanes | |
| JP7153337B2 (ja) | スピロシロキサン化合物、主鎖中にスピロシロキサン構造を有する定序性ポリシロキサン及びそれらの製造方法 | |
| JPH08157483A (ja) | 有機ケイ素化合物およびその製造方法 | |
| JP7107636B2 (ja) | シクロジエン添加剤を使用する白金触媒ヒドロシリル化反応 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20040609 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20040615 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20040915 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20040921 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20041215 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20051108 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20051208 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091222 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101222 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101222 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111222 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111222 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121222 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121222 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131222 Year of fee payment: 8 |
|
| EXPY | Cancellation because of completion of term |